Iwan & Ries Co.

Since 1857, this shop has been a go-to for all of Chicago's tobacco enthusiasts, and is one of the oldest family-owned tobacconists in the country. The shop boasts over 15,000 pipes in stock, hundreds of cigars, and countless accessories. Be sure to check out the adjoining smoking lounge, which offers an old-school vibe, free wi-fi, a board room and is BYOB.